1. Field of the Invention
The present invention relates to an oxidation catalyst and methods using the same for producing carbonyl compounds and hydroxy adduct compounds by oxidative cleavage of an olefinic double bond or addition reaction thereto.
A method for producing adipic acid by reacting, in the presence of sodium tungstate and trioctylmethylammonium sulfate, cyclohexene with an aqueous hydrogen peroxide is known (JP-A 2000-86574), and a method for producing an aldehyde by reacting an olefin with hydrogen peroxide, using heteropolyacid containing phosphorus or germanium, is also known (JP-B 6-84324).
However, yields of the desired products in these methods were not always satisfactory for an industrial scale of production.
According to the present invention, carbonyl compounds and hydroxy adduct compounds can be obtained by using a readily available oxidation catalyst, which can selectively provide desired compounds in an improved yield.
Thus, the present invention provides:
1. a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound,
which comprises
reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from
(a) tungsten,
(b) molybdenum or
(c) a tungsten or molybdenum metal compound comprising
(ia) tungsten or (ib) molybdenum and
(ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen;
2. an oxidation catalyst composition obtained by reacting aqueous hydrogen peroxide with at least one member selected from
a tungsten or molybdenum metal compound comprising
(ia) tungsten or (ib) molybdenum, and
(ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen,
provided that said tungsten metal compound is not tungsten carbide;
3. an oxidation catalyst composition obtained by
reacting aqueous hydrogen peroxide with at least one member selected from
(a) tungsten,
(b) molybdenum, or
(c) a tungsten or molybdenum metal compound comprising
(ia) tungsten or (ib) molybdenum, and
(ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen,
and containing an organic solvent;
4. a method for producing a carbonyl compound of formula (II):
RaRbCxe2x95x90Oxe2x80x83xe2x80x83(II),
wherein a and b respectively represent 1 and 2, or 3 and 4, which comprises subjecting a hydroxy adduct compound of formula (III):
Xxe2x80x94(R1)(R2)Cxe2x80x94C(R3)(R4)OHxe2x80x83xe2x80x83(IIIa)
wherein X is a hydroperoxide group, and R1 to R4 represent a hydrogen atom or an organic residue, to a decomposition reaction;
5. a method for producing a hydroxy adduct compound of formula (IIIb):
Xxe2x80x94(R1)(R2)Cxe2x80x94C(R3)(R4)OHxe2x80x83xe2x80x83(IIIb)
wherein X is a hydroxy group and R1 to R4 independently represent a hydrogen atom or an organic residue, which comprises reacting a hydroxy adduct compound of formula (IIIa):
Xxe2x80x94(R1)(R2)Cxe2x80x94C(R3)(R4)OHxe2x80x83xe2x80x83(IIIa)
wherein X is a hydroperoxide group, and R1 to R4 are the same as defined above, with a reducing agent;
6. a hydroxy adduct compound of formula (III):
Xxe2x80x94(R1)(R2)Cxe2x80x94C(R3)(R4)OHxe2x80x83xe2x80x83(III)
wherein X is a hydroperoxide group or a hydroxy group, R1 and R2 represent a methyl group, R3 represents a hydrogen atom, and R4 represents a group of formula: 
wherein Rxe2x80x2 is an alkyl, aryl or aralkyl group, and
7. a hydroxy adduct compound of formula (IIIa):
Xxe2x80x94(R1)(R2)Cxe2x80x94C(R3)(R4)OHxe2x80x83xe2x80x83(IIIa)
wherein X represents a hyroperoxide group, R1 represents a methyl group, R3 represents a hydrogen atom, and R2 and R4 form a group of formula: 